Organopolysiloxane compounds have excellent interface properties, such as thermal stability, water repellency, defoaming properties, and releasability, and thus are frequently used in various fields. Particularly, in recent years, because of the utilizing of their specific interface properties, uses as coating forming agents have expanded. In addition, the applications as modifiers for providing the temperature properties and interface properties of the organopolysiloxane compounds to various resins have also been actively developed.
In other words, for example, dimethylpolysiloxane, methylphenylpolysiloxane, fatty acid-modified polysiloxanes, and polyether-modified polysiloxanes have been conventionally used for the improvement of the performance of synthetic resins, such as paints and molded compounds. However, the range of use has been limited because these have insufficient compatibility with resins and insufficient heat resistance.
In order to solve these problems, various reactive polysiloxane compounds, for example, low-molecular-weight dimethylsiloxane compounds having a functional group, such as an epoxy group, an amino group, a hydroxyl group, or a (meth)acryl group, at molecular end group are commercially available. In addition, reaction products of these and other resins, for example, reaction products of terminal epoxy group-containing polysiloxanes and phenolic resins (Patent Document 1, Patent Document 2, and the like), and reaction products of terminal hydrogen group-containing polysiloxanes and alkenyl group-containing epoxy resins (Patent Document 3 and the like) are proposed.
In recent years, polysiloxane compounds having a controlled structure and having any number of functional groups in the molecule have been eagerly desired as resist materials having submicron resolution capability required for the production of VLSIs, as modifiers for the mechanical properties, moisture resistance, surface properties and the like of various thermosetting resins and thermoplastic resins, and as separation membranes and biocompatible polymer materials. But, in the above-described processes, a disadvantage of the processes using commercially available low-molecular-weight dimethylsiloxane compounds having a functional group in the molecule is insufficient compatibility with other resins. Thus, it results in a decrease in molding processability and mechanical strength. In addition, the processes using reaction products of polysiloxanes having a functional group at an end and other resins are that undesirable phenomena, such as abnormal thickening and gelation, are likely to occur during the modification reaction, and unreacted components remain, resulting in a decrease in compatibility, and so on.
Therefore, for the purpose of producing a phenol structure-introduced, modified polysiloxane compound having a controlled molecular weight and structure and having a narrow molecular weight distribution, the applicants have developed a method of polymerizing a compound in which the phenolic hydroxyl group of p-alkenylphenol is protected by a saturated aliphatic protecting group by an anionic polymerization technique, then adding a cyclic siloxane compound for copolymerization, and then eliminating the saturated aliphatic protecting group (Patent Document 4).
Prior Art Documents
Patent Documents
    Patent Document 1: Japanese Unexamined Patent Application Publication No. 61-73725    Patent Document 2: Japanese Unexamined Patent Application Publication No. 62-174222    Patent Document 3: Japanese Unexamined Patent Application Publication No. 62-212417    Patent Document 4: Japanese Patent No. 3471010